Method of preparing stabilized organic sulfur-containing compounds



Patented Feb. 1950- sr'r E METHOD OF PREPARING ZED ORGANIC SUL-CUNTEOUNDS No Drawing. Application may 31, 1946 Serial No. erases 11 Claims.(or. ass-sa This invention relates to an improved method of inhibitingthe evolution of hydrogen sulfide from organic sulfur-containingcompounds from which hydrogen sulfide is normally evolved, and toorganic sulfur-containing compounds stabilized against hydrogen sulfideevolution.

Many organic sulfur-containing compounds evolve hydrogen sulfide in thecourse of their normal use or in storage. Because of the obnoxious odorof hydrogen sulfide gas the evolution of hydrogen sulfide from suchorganic compounds is very objectionable. Examples of such organiccompounds are sulfurized terpenes. sulfurized olefins and olefinpolymers, sulfurized fatty oils of animal and vegetable origin,sulfurized sperm oil, sulfurized mineral oils and the like. Not only isthe use of such organic com pounds restricted because of the obnoxiousodor given off by the evolved hydrogen sulfide, but the use of compoundscontaining various amounts of such organic sulfur compounds is oftenrestricted because of this nuisance. For example, lubricants such aslubricating oils frequently contain sulfurized materials to impartthereto various desired properties such as extreme pressure properties,anti-corrosion properties and the like. However, such lubricants duringservice evolve hydrogen sulfide which is found highly objectionable bythe users of such lubricants. It is therefore an object of the presentinvention to provide an improved method of inhibiting the evolution ofhydrogen sulfide from or-. ganic sulfur containing compounds whichnormally evolve hydrogen sulfide during service or storage. Anotherobject of the present invention is to provide a method whereby organicsulfur-containing compounds which evolve obnoxious hydrogren sulfideodors are rendered substantially inoffensive. Another object of theinvention is to provide organic sulfur-containing compounds stabilizedagainst hydrogen sulfide evolution. Other objects and advantages of theinvention will become apparent from the following description thereof.

-'We have discovered that the evolution of hydrogen sulfide from organicsulfur-containing compounds can be substantially inhibited by adding tosuch sulfur-containing compounds 9. qulnone in small but sufilcientquantities to substantially inhibit the evolution of hydrogen sulfide;suitably in concentrations of from about 0.001% to about 4%, andpreferably from about 0.01% to about 2%. The term quinone as used hereinand in the appended claims includes monoand poiynuclear quinones such asbenzoquinone, naphthoquinones, anthraquinones. Dhenanthraduinone,camphor-quinone and addition prodnets and substituted derivativesthereof. The term qulnone" also includes isomers of such quinones. Thequinones may contain substitution groups such as halogens, amino, alkyl,aryl, alkaryl, aralkyl, alkoxy, aroxyl, hydroxy and other substituentgroups.

The following specific compounds are repre sentative of the classesnamed above:

Para-benzoquinone Ortho-benzoquinone 2,6-dimethoxybenzoquinone1,2-dimethyl-4,5-benzoquinone Toluquinone Xyloquinones Quinone haloidsMono chloroquinone Dichloroquinones MethylanthraquinonesAcenaphthene-quinone Phenanthraquinone Aminoquinone DiphenoquinoneMethoxynaphthoquinones 1,4-naphthoquinone 1,2-naphthoquinone 2,6-naphthoquinone Camphor-quinone Amphi-chrysene-quinone Pyrene-quinoneWhile the foregoing compounds are all eifec= tive in inhibiting theevolution of hydrogen sulfide from organic sulfur-containing compounds,it is not to be implied that all are equivalents, since the specificactivity of the various quinones varies to some extent. We prefer toemploy the unsubstituted quinones.

The effectiveness of quinones in inhibiting the evolution of hydrogensulfide from organic su1- fur-containing compounds is illustrated by thedata in the following table. To obtain these data the control which wasa mineral lubricating oil additive composition containing a KOHneutralized reaction product of P255 and an isobutylene polymer. asulfurized mineral oil and a sulfurized terpene, was placed in a,container and maintained at a temperature of 200 F. while passingnitrogen through at a rate of one liter per hour. After one-half hour toremove preformed hydrogen sulfide, the exit tube was connected to aflask containing a lead acetate solution. The rate of hydrogen sulfideevolved was determined trol and the control containing one percent (a)para-benzoquinone, (b) anthraquinone, and (c) 1,2-naphthoquinone weresubjected to this test.

The above data show the efiectiveness of quinones in inhibitin hydrogensulfide evolution from organic sulfur-containing compounds.

While we have described our invention by reference to specificembodiments thereof, these have been by way of illustration, and theinvention is not to be limited thereby but includes within. its scopesuch modifications as come within the spirit of the appended claims.

We claim:

1. The method of inhibiting the evolution of hydrogen sulfide from asulfurized oleaginous compound which evolves hydrogen sulfide,comprising adding to said compound from about 0.001% to about 4% of aquinone to substantially inhibit the evolution of hydrogen sulfide.

2. The method of inhibiting the evolution of hydrogen sulfide from asulfurized oleaginous compound which evolves hydrogen sulfide,comprising adding to said compound from about 0.001% to about 4% of abenzoquinone to substantially inhibit the evolution of hydrogen sulfide.

3. The method described in claim 2 in which l I 4 subetsntislly inhibitthe evolution of hydrogen sulfide.

5. The method or inhibiting the evolution 0! hydrogen sulfide from asulfurized oleaginous compound which evolves hydrogen sulfide,comprisingpadding to said compound from about 0.001% to about 5% oi. anaphthoquinone to inhibit the evolution of hydrogen sulfide.

8. The method described in claim 5 in which the naphthoquinone is1,2-naphthoquinone.

7. The method of inhibiting the evolution of hydrogen sulfide from asulfurized oleaginous compound which evolves hydrogen sulfide,comprising adding to said compound from about 0.001% to about 4% of ananthroquinone to substantially inhibit the evolution of hydrogensulfide.

8. The method of inhibitingthe evolution of hydrogen sulfide from alubricating oil composition containing a sulfurized oleaginous compoundwhich normally evolves hydrogen sulfide in storage, comprisingincorporating in said lubricating oil composition from about 0.001% toabout 4% of a qulnone to substantially inhibit the evolution of hydrogensulfide.

9. The method as described in claim 8 in which the quinone isabenzoquinone.

10. The method as described in claim 8 in which the quinone is anaphthoquinone.

11. The method as described in claim 8 in which the quinone is ananthraquinone.

EDWARD N. ROBERTS. LAWSON W. MIXON.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 2,267,142 Smith Dec. 23, 19412,3673% Evans Jan. 16, 1945

1. THE METHOD OF INHIBITING THE EVOLUTION OF HYDROGEN SULFIDE FROM ASULFURIZED OLEAGINOUS COMPOUND WHICH EVOLVES HYDROGEN SULFIDE,COMPRISING ADDING TO SAID COMPOUND FROM ABOUT 0.001% TO ABOUT 4% OF AQUINONE TO SUBSTANTIALLY INHIBIT THE EVOLUTION OF HYDROGEN SULFIDE.